Novel chiral recognition elements for molecularly imprinted polymer preparation

Area of Science:

• Chiral chemistry
• Polymer science
• Analytical chemistry

Background:

• Molecular imprinting (MI) is a powerful technique for creating polymers with specific recognition sites.
• Developing chiral selectors for enantioselective separations remains a significant challenge in analytical chemistry.
• Chiral functional monomers are crucial for imparting stereospecificity in imprinted polymers.

Purpose of the Study:

• To introduce a novel chiral functional monomer system for molecular imprinting.
• To investigate the ability of this system to create polymers with enhanced ligand-binding capacities and stereoselectivity.
• To evaluate the performance of the imprinted polymers in separating chiral molecules.

Main Methods:

• Synthesis of a novel chiral monomer: dibenzyl (2R,3R)-O-monoacryloyl tartrate.
• Utilizing the monomer's hydroxyl group for directed template-monomer interactions during polymerization.
• Deprotection of benzyl ester groups to yield carboxylate recognition sites.
• Applying the molecular imprinting technique to cinchonidine alkaloids (+)-cinchonine and (-)-cinchonidine.

Main Results:

• The developed monomer system successfully created molecularly imprinted polymers (MIPs).
• The imprinted polymers exhibited stereoselective binding towards the target alkaloids.
• Imprinting with (+)-cinchonine resulted in a polymer that reversed the inherent chiral selectivity of the monomer matrix.
• The deprotection step enhanced the ligand-binding capacity of the recognition sites.

Conclusions:

• The novel chiral functional monomer system is effective for creating highly stereoselective MIPs.
• This system offers a promising approach for enantioselective separation applications.
• The ability to reverse inherent chiral selectivity opens new avenues in chiral recognition material design.